2-Methoxyethylamine → HCID 28400019, compound

HRID 2390877Notes

Reaction equation

HRID 2390877 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[CH3:11][O:12][CH2:13][CH2:14][NH2:15]>CC(O)C>[CH3:11][O:12][CH2:13][CH2:14][NH:15][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 792226-Chloronicotinic acid

Product 1

HCID 28400019HCID 28400019, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A microwave vial is charged with 6-chloronicotinic acid (1 g, 6.35 mmol), 2-methoxyethylamine (1.214 mL, 13.96 mmol) and IPA (3.5 mL) sealed and irradiated in a microwave synthesizer at 180° for 40 min. The reaction was cooled, concentrated and purified by SiO2 chromatography eluting with a MeOH/DCM gradient (5% to 10% MeOH containing 0.5% HOAc) to afford 0.24 g of 6-(2-methoxy-ethylamino)-nicotinic acid (330) as a white solid.

Workup

  1. customsealed
  2. customirradiated in a microwave synthesizer at 180° for 40 min
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. custompurified by SiO2 chromatography
  6. washeluting with a MeOH/DCM gradient (5% to 10% MeOH containing 0.5% HOAc)

Sources & evidence

ORD record
ord-a3846bd482974b03bdbd5d4ce3b79840
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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